How many flights depart from Orlando to Chicago on average per week?

As of September 2025, 458 flights take off from Orlando and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What is the cheapest airline that flies from Orlando to Chicago?

Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Orlando to Chicago

What airlines fly to Chicago?

Frontier, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Orlando according to our data. Frontier is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Orlando to Chicago on average per day?

As of September 2025, there are 65 flights per day flying from Orlando to Chicago. The most common time of day flights depart is 7:00AM, with 49% of flights taking off in the afternoon.

When did momondo last update prices for flights from Orlando to Chicago?

Prices for flights from Orlando to Chicago refresh daily.

How many operators does momondo search for flights from Orlando to Chicago?

The number of operators available for flights from Orlando to Chicago is 7 as of September 2025.

How old do you have to be to fly from Orlando to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$50 Cheap Flights from Orlando to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Orlando and Chicago?

Prices are currently typical for flights on this route. Typical prices usually range from $87 to $240. The lowest price recently found on this route was $87.

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Find the cheapest flights from Orlando to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

$87Frontier

Find Deal

Thu, Oct 2 - Sun, Oct 5

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

$88Frontier

Find Deal

Fri, Oct 3 - Mon, Oct 6

1:02 pm - 3:17 pmMCO-ORD

3h 15mnonstop

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

$89Frontier

Find Deal

Sat, Sep 27 - Mon, Sep 29

6:05 am - 8:14 amMCO-ORD

3h 09mnonstop

6:58 pm - 10:50 pmORD-MCO

2h 52mnonstop

$90

Find Deal

Thu, Oct 9 - Tue, Oct 14

2:43 pm - 4:57 pmMCO-ORD

3h 14mnonstop

6:00 am - 9:44 amORD-MCO

2h 44mnonstop

$96

Find Deal

Thu, Oct 16 - Sun, Oct 19

12:33 pm - 2:18 pmSFB-RFD

2h 45mnonstop

7:47 pm - 11:17 pmRFD-SFB

2h 30mnonstop

$97Allegiant Air

Find Deal

Fri, Oct 10 - Mon, Oct 13

7:50 pm - 9:58 pmMCO-ORD

3h 08mnonstop

6:00 am - 9:44 amORD-MCO

2h 44mnonstop

$98Spirit Airlines

Find Deal

Tue, Sep 30 - Tue, Oct 7

7:30 pm - 9:33 pmMCO-ORD

3h 03mnonstop

7:51 pm - 11:43 pmORD-MCO

2h 52mnonstop

$99Spirit Airlines

Find Deal

Thu, Oct 9 - Mon, Oct 13

6:15 am - 8:00 amSFB-RFD

2h 45mnonstop

8:50 am - 12:20 pmRFD-SFB

2h 30mnonstop

$112Allegiant Air

Find Deal

Wed, Oct 1 - Wed, Oct 8

5:50 pm - 7:35 pmMCO-MDW

2h 45mnonstop

5:00 am - 8:30 amMDW-MCO

2h 30mnonstop

$158Southwest

Find Deal

Wed, Oct 22 - Mon, Oct 27

Frontier flights from Orlando to Chicago

Our best Frontier deals on Orlando to Chicago flight tickets

Frontier

Oct 2

MCO5:24 pmOrlando

3h 20m

ORD7:44 pmChicago O'Hare Intl

Oct 5

ORD8:49 pmChicago O'Hare Intl

2h 46m

MCO12:35 amOrlando

$87

Find similar

Frontier

Oct 3

MCO5:24 pmOrlando

3h 20m

ORD7:44 pmChicago O'Hare Intl

Oct 6

ORD8:49 pmChicago O'Hare Intl

2h 46m

MCO12:35 amOrlando

$88

Find similar

Frontier

Sep 27

MCO1:02 pmOrlando

3h 15m

ORD3:17 pmChicago O'Hare Intl

Sep 29

ORD8:49 pmChicago O'Hare Intl

2h 46m

MCO12:35 amOrlando

$89

Find similar

Spirit Airlines flights from Orlando to Chicago

Our best Spirit Airlines deals on Orlando to Chicago flight tickets

Spirit Airlines

Sep 30

MCO7:50 pmOrlando

3h 08m

ORD9:58 pmChicago O'Hare Intl

Oct 7

ORD6:00 amChicago O'Hare Intl

2h 44m

MCO9:44 amOrlando

$98

Find similar

Spirit Airlines

Oct 9

MCO7:30 pmOrlando

3h 03m

ORD9:33 pmChicago O'Hare Intl

Oct 13

ORD7:51 pmChicago O'Hare Intl

2h 52m

MCO11:43 pmOrlando

$99

Find similar

Spirit Airlines

Sep 25

MCO2:07 pmOrlando

3h 05m

ORD4:12 pmChicago O'Hare Intl

Sep 29

ORD6:30 amChicago O'Hare Intl

2h 43m

MCO10:13 amOrlando

$100

Find similar

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/2

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Sun 10/5

8:49 pm-12:35 am

Nonstop2h 46m

$87

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 10/3

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 10/6

8:49 pm-12:35 am

Nonstop2h 46m

$88

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/27

1:02 pm-3:17 pm

Nonstop3h 15m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-12:35 am

Nonstop2h 46m

$89

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/9

6:05 am-8:14 am

Nonstop3h 09m

Chicago O'Hare Intl

Tue 10/14

6:58 pm-10:50 pm

Nonstop2h 52m

$90

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/16

2:43 pm-4:57 pm

Nonstop3h 14m

Chicago O'Hare Intl

Sun 10/19

6:00 am-9:44 am

Nonstop2h 44m

$96

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 10/10

12:33 pm-2:18 pm

Nonstop2h 45m

Chicago Greater Rockford

Mon 10/13

7:47 pm-11:17 pm

Nonstop2h 30m

$97

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/30

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 10/7

6:00 am-9:44 am

Nonstop2h 44m

$98

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 10/9

7:30 pm-9:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Mon 10/13

7:51 pm-11:43 pm

Nonstop2h 52m

$99

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 10/1

6:15 am-8:00 am

Nonstop2h 45m

Chicago Greater Rockford

Wed 10/8

8:50 am-12:20 pm

Nonstop2h 30m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 10/22

5:50 pm-7:35 pm

Nonstop2h 45m

Chicago Midway

Mon 10/27

5:00 am-8:30 am

Nonstop2h 30m

$158

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How to get the cheapest flight ticket from Orlando to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Orlando and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Orlando, with most prices found around $148. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Orlando to Chicago during August average around $159.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $236. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando to Chicago for around $451.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando to Chicago during this time can be as low as $239. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $576.

What is the cheapest Orlando to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $220 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as $176 on momondo.

What cabin class options are available on Orlando to Chicago flights?

There are 4 cabin classes available to choose from on Orlando to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Orlando to Chicago flight prices changed over time?

As of September 2025, prices for Orlando to Chicago flights are approximately 17% more expensive when compared to flights at the same time last year.

When to book flights from Orlando to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Best Price Found	$79
Fastest flight time	2h 42m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Orlando in the past 72 hours is $79. The best round-trip flight deal from Orlando to Chicago found on momondo in the last 72 hours is $106.

The fastest flight from Orlando to Chicago takes 2h 42m

Direct flights go from Orlando to Chicago every day.

There are 2 airports near Chicago: Chicago Greater Rockford (RFD), Chicago Midway (MDW)

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How far is Orlando to Chicago by plane?
Chicago is 985.3 mi away from Orlando. 2h 42m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando to Chicago?
Prices for flights from Orlando to Chicago refresh daily.
How many operators does momondo search for flights from Orlando to Chicago?
The number of operators available for flights from Orlando to Chicago is 7 as of September 2025.
How old do you have to be to fly from Orlando to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Orlando to Chicago?
Based on momondo bookings for flights between Orlando and Chicago, the leading plane model is Airbus A321-100/200, making up 15.26% of the total bookings. Other popular models include Airbus A321neo with 14.11%, Airbus A321 (sharklets) with 11.69%, and Airbus A320neo with 9.94%.
What is the most popular airline from Orlando to Chicago?
momondo data reveals that the most frequently booked airline on the route from Orlando to Chicago is Frontier, representing 52% of all bookings. The subsequent popular airlines are Spirit Airlines at 16%, American Airlines at 16%, and Southwest at 9%.

Best airlines flying from Orlando to Chicago

Compare and see reviews for airlines that fly from Orlando to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $72	Free Cancellation	Rating 5.8 3,172 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $73	Free Cancellation	Rating 6.3 8,015 reviews	Search Spirit Airlines flights
Allegiant Air	PriceFrom $90	Free Cancellation	Rating 7.2 699 reviews	Search Allegiant Air flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 7,954 reviews	Search Delta flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 8,929 reviews	Search United Airlines flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $159	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights

Southwest Flights From Orlando to Chicago
Southwest is one of the most popular airlines flying from Orlando to Chicago, operating 65 flights/week on average for this route. A good Southwest flight deal for Orlando to Chicago starts from $159 round-trip, up to an average price of $298. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Orlando to Chicago
$158 is the best United Airlines flight deal from Orlando to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $346, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,929 user reviews) flies into Chicago from Orlando 62 times in an average week so prices can vary.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Orlando to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Orlando to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Orlando to Chicago with flexible booking policies on momondo?

Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Orlando to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Orlando.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Orlando are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.